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Lecture on Organic Chemistry Part 2

OVERVIEW OF ORGANIC COMPOUNDS

REVIEW OF PART 1

OVERVIEW OF ORGANIC COMPOUNDS

 Made up of hydrocarbons
 If other atoms or grp of elements attached
to these hydrocarbons, it will be changing
the structure of that organic molecule, as
well as its reactivity = FUNCTIONAL
GROUPS
 Different Representations of Organic Molecules
 Structural Formula
 Condensed Formula
 Line-angle notations
INTRODUCTION TO THE REACTIONS OF CARBON
 Classifications or Examples of Organic Molecules
 Addition Reactions
 Elimination Reactions
 Substitution Reactions
 Oxidation Reactions
 Reduction Reactions
 Isomerization
- can be created if there is a presence
energy (heat) that can change the
orientation of a certain organic
molecule
NOMENCLATURE, PROPERTIES, AND HEALTH-RELATED
APPLICATIONS OF ALKANES AND ALKENES
 IUPAC Rules/Names
 Trivial or Common Names
 Vaseline and Mineral Oil for Health Applications
 The presence of polymerization in surgical gloves,
blood bags, and tubings in the laboratory
ALKYNES
 Second group of hydrocarbons that are unsaturated
 Saturated – maximum amount of atoms;
sigma bonds
 Unsaturated – with hydrogen deficiency; pi
bonds (double and triple)
 Alkenes – double bond
 Alkynes – triple bond (1 bond is
sigma, 2 bonds are pi bond)
- The presence of pi bond is very
important in the reactivity of organic
molecules due to its high e- density
- They are capable of donating e-
interacting w/ other atoms in a certain
reaction
NOMENCLATURE OF ALKYNES
1. The “yne” suffix indicates an alkyne
2. The longest chain chosen for the root name must include
both carbon atoms of the triple bond
3. The root name must be numbered from the end nearest a
triple bond carbon atom. If the triple bond is in the center of
the chain, the nearest substituent is used to determine the
end where numbering starts.
4. If several multiple bonds are present, each must be
assigned to a locator number. Double bonds precede triple
bonds in the IUPAC name, but the chain is numbered from
the end nearest the multiple bond, regardless of its nature
Examples:
FOR HYDROCARBONS CONTAINING BOTH TRIPLE AND
DOUBLE BONDS:
 The priority for number is the DOUBLE BOND
 Carbon atoms from the left portion: 5 carbon atoms
 Root name: pent
 The lower number of low cant must be provided
under the double bond
 The triple and double bonds are on the opposite
ends
 Numbering:
- no. 1 and 2 carbon atoms must be in
the double bond = PRIORITY/
designation of the lowcant
- no. 3 carbon atom must be in the single
bond
- no. 4 and 5 carbon atoms must be in
the triple bond
 A functional group with a high reactivity is the basis
for naming the organic compound = PRIORITY
PHYSICAL PROPERTIES OF ALKYNES
 Alkynes are insoluble in water but soluble (polar,
ionic) in organic solvents, have densities less than
that of water, and have boiling points that increase
w/ molecular mass
 Presence of double bond – high bonding of
one carbon atom to another c atom
 Presence of triple bond – low bonding of
one carbon atom to another c atom
 Breakage of cpds will be easier in single
bonds than in double and triple bonds
 Low-molecular-mass alkynes are gases at room
temperature
CHEMICAL PROPERTIES OF ALKYNES
 Created by the presence of the pi bond = reactivity
of alkynes w/ other components
Hydrogenation of an alkyne
 Associated w/ the idea of ADDITION (like in alkene)
- Unsaturated to saturated
 3. Lecture on Organic Chemistry Part 2
o Nickel as the catalyst added with hydrogen will lead
to the conversion of alkyne to alkene, and alkene to
alkane (further addition)
o It is addition reaction because carbon is attached to
a higher number of substituent or atoms
Halogenation of an alkyne
o Similar w/ the bromination reaction
- bromine in water or carbon tetrachloride is reddish
brown in color wherein if we add bromine solution in
a hydrocarbon solution containing pi bonds, it will
bind w/ the halogen
- binding of alkyne and hydrocarbons w/ double and
triple bonds can promote decoloration of the
bromine solution
- it will result to discoloration or disappearance of
color of the solution
- the bromine used to be attached w/ water but due
to the presence of pi bonds, the bromine attached
itself to the hydrocarbon causing discoloration of
bromine solution from reddish brown to no color at
all
o Further addition reaction of alkyne will convert:
ALKYNE  ALKENE ; ALKENE ALKANE
Hydrohalogenation of an alkyne
 Both hydrogen and halogen
 Commonly bromine, flourine, and chlorine
 Further hydrogenation will lead to the formation of
alkane
 In cases of alkenes together with alkynes, since they
contain pi bonds, their chemical reaction is more on
ADDITION REACTION from
 unsaturated state to saturated sate
 from hydrocarbons with double and triple
bonds to hydrocarbons with single bond
AROMATIC HYDROCARBONS
 hydrocarbons capable of delocalization of electrons
 the e- are not a property of only one carbon
atom
 in a cyclic form
 based on theories, they are sp2 hybridized since they
have double bonds
 the carbon atoms can promote the movement of e-
from one atom to another. It may promote changes
w/ their distribution but still located w/in a one
molecule
 circle: e- are equally distributed in an entire
molecule
 Aromatic ring system is a highly unsaturated carbon
ring system in w/ch both localized and delocalized
bonds are present
 Carbon atoms are hydrogen deficient
 Can move fr. one carbon atom to another
 Unique feature: this delocalization of the e-
will make their structure very stable
 Associated w/ the presence of pi bonds
- usually unstable & very reactive in a
cyclic form due to resonance or
delocalization distribution of the e- in
the entire molecule
 Delocalized bond is a covalent bond in w/c electrons
are shared among more than two atoms
- Sharing of e- fr. one carbon atom to
another
 Resonance effect – donation or withdrawal of
electrons through orbital overlap with neighbouring
pi bonds
 there is a movement of e- in the entire molecule
(delocalization)
 this is important in maintaining their stability
 sp2 hybridized carbon
 unstable and reactive, but due to resonance, they
become stable
 since they are very stable, they are only subjected to
SUBSTITUTION REACTIONS
 even though it has double bond (can have addition;
unsaturated to saturated) but it’s different in
aromatic hydrocarbons
- they are very stable due to
delocalization of other electrons w/in
that molecule, in all carbon atoms the
electron is owned by all
 we have hormones in our body containing aromatic
hydrocarbons that are very stable, w/c is good
because they are not easy to break
 Aromaticity – delocalization of electrons w/in a
certain (aromatic) hydrocarbon
NOMENCLATURE
BENZENE DERIVATIVES WITH ONE SUBSTITUENT
The IUPAC system of naming monosubstituted benzene
derivatives uses the name of the substituent as a prefix to the
name benze
 We don’t need to utilize a number
- The rotation of carbons has the same
possibility to be carbon 1 (w/ an
attached substituent)
- Doesn’t need to place a locant because
1 is already the location of the
substituent
 C6H6
A few monosubstituted benzenes have names wherein the
substituent and the benzene ring taken together constitute a
new parent name. Two important examples of such
nomenclature w/ hydrocarbon substituents are:
 3. Lecture on Organic Chemistry Part 2
For monosubstituted benzene rings that have a group
attached that is NOT easily named as a substituent, the
benzene ring is often treated as a group attached to this
substituent
 The benzene ring attachment is called a phenyl
group, and the compound is named according to the
rules for naming alkanes, alkenes, and alkynes
BENZENE DERIVATIVES WITH TWO SUBSTITUENTS
If there are 2 substituent, we will utilize 1 as a main point
Benzene derivatives w/ 2 substituents, we can utilize
numbers or other representations
Difference in the location of Numbers or non-numerical
the substituent prefixes
2 carbon atoms Ortho
3 carbon atoms Meta
4 carbon atoms Para
Specify the positions of the substituents relative to one
another. This can be done in either of two ways: by using
numbers or non-numerical prefixes
Examples
When one of the two substituents in a disubstibuted benzene
imparts a special name to the compound, the compound is
named as a derivative of that parent molecule. The special
substituent is assumed to be at ring position 1
When neither substituent group imparts a special name, the
substituents are cited in alphabetical order before the ending
–benzene. The carbon of the benzene ring bearing the
substituent with alphabetical priority becomes carbon 1
A benzene ring bearing two methyl groups is a situation that
generates a new special base name. Such compounds (there
are three isomers) are not named as dimethylbenzenes or as
methyl toluenes. They are called xylenes (common reagent
used in tissue processing)
BENZENE DERIVATIVES WITH THREE OR MORE SUBSTITUENT
When more than two groups are present on the benzene
rings, their positions are indicated with numbers
 The ring is numbered in such a way as to obtain the
lowest possible numbers for the carbon atoms that
have substituents
 If there is a choice of numbering systems (two
systems give the same lowest set), then the group
that comes first alphabetically is given the lower
number
PYSICAL PROPERTIES OF HYDROCARBONS
 They are insoluble in water, are good solvents
for other nonpolar materials, and are less dense
than water
- Not capable of forming hydrogen bond
w/ water
- Our body is made of 50%+ of water
(important in biochemical reactions)
- If a certain substance present in the
body is capable of hydrogen bonding, it
will be soluble in water. But if it is not
capable of forming hydrogen bond, it
will not dissolve in water – this is
important
 If an aromatic hydrocarbon
hormone is polar dissolves in
water, it will lose its purpose
CHEMICAL PROPERTIES OF HYDROCARBONS
 Only capable of SUBSTITUTION, not ADDITION
or ELIMINATION
Alkylation of Benzene
 Includes the presence of a salt or a an alkyl
group (alkene – 1 hydrogen) attached to a
halogen
 Can happen when 1 hydrogen is removed, and
alkyl group binds. The hydrogen removed will
move to the other side (hydrogen is implied) =
SUBSTITUTION
Halogenation of Benzene
 Addition of Chlorine or Bromine
 We use Iron as a catalyst
 SUBSTITUTION will take place
 Further substitution makes hydrocarbons more
stable to be functional
 3. Lecture on Organic Chemistry Part 2

Fused-Ring Aromatic Hydrocarbons and Cancer

 If a hydrocarbon is exposed/subjected to
combustion, it can produce a certain amt of fused-
ring aromatic hydrocarbons
Example:
1. Tobacco/cigarette smoking
2. Grilling used charcoal
3. Vehicle

ELECTROHIPLIC AROMATIC SUBSTITUTION

 A part of an organic cpd that is electron
deficient; low electron density

General Mechanism
 Combination of ADDITION and ELIMINATION
Step 1: Addition of the electrophile to the benzene ring
using the pi bond electron, leading to the loss of aromaticity
or delocalization due to the creation of charge
 The nucleophile is the pi bond (partial positive
or neutral)
 First step: ADDITION OF ELECTROPHILE TO BIND
W/ THE BENZENE RING USING PI BOND E- THAT
WILL INTERACT W/ THE ELECTROPHILE
- will attach to the benzene ring =
aromaticity/delocalization will removed
- other part will become negatively
charged
- ADDITION will lead to loss of
aromaticity
 Second step: ELIMINATION (loss of proton)
- Uranium ion (positive charge)
Step 2: Elimination or loss of a proton
 To have a more appropriate aromaticity
 Carcinogenic
- can affect the mechanism/ machinery of a cell,
losing control of its growth
- made up of 4 or more fused-ring aromatic
hydrocarbons
- these bold parts has a structure that can bind and
affect the growth of cells causing APOPTOSIS
(programmed cell death)
- one mechanism of cancer is there are substances
that will destroy the apoptotic mechanism, causing a
rapid growth of cell leading to the creation of
dysfunctional CANCER CELLS capable of fast and
abnormal proliferation
 3,4-Benzpyrene
- most common
- came from cigarette smoking (lip cancer,
nasopharyngeal carcinoma, lung cancer)
- due to burning/combustion, the hydrocarbons
become fused ring aromatic hydrocarbons (has a
part that can cause cancer by disrupting the usual
cell mechanisms that can lead to the formation of
abnormal, dysfunctional, and fast proliferating cells
*Not all aromatic hydrocarbons in our body are harmful.
- we have hormones in our body that are needed to
be in a state of aromatic hydrocarbon for their
stability

SUMMARY:
Unsaturated Hydrocarbons Saturated Hydrocarbons
Akenes Alkanes
HEALTH APPLICATION OF AROMATIC HYDROCARBONS (unstable pi bonds)
Fused-Ring Alkynes
A fused-ring aromatic hydrocarbon is an aromatic (unstable pi bonds)
hydrocarbon whose structure contains two or more rings Aromatic Hydrocarbons
fused together. Two carbon rings that share a pair of carbon (stable pi bonds)
atoms are said to be fused.
 Naphthalene
 Anthracene
 Phenanthrene
 3. Lecture on Organic Chemistry Part 2

FUNCITONAL GROUPS
 A group of atom/s that can be attached to a large
molecule or hydrocarbon that can dictate its own
property
 Small portion attached to a large molecule that can
change the entire nature of that large molecule
 Dictate the property of organic cpds
 Two things to consider in describing reactivity of
hydrocarbons/organic cpds:
1. Check for the presence of pi bonds (single,
double/saturated, unsaturated)
2. Check for the presence of functional groups

FUNCTIONAL GROUPS W/ CARBON-OXYGEN DOUBLE BOND

(CARBONYL GROUPS)

FUNCTIONAL GROUPS W/ CARBON-CARBON MULTIPLE

BONDS
 The presence of pi bond or color red
Examples:
- indicates high amount of e- density and reactivity
1. Aldehyde
Examples:
-carbon contains double bond to oxygen; single
1. Alkene
bonds to carbon and hydrogen
-Addition and Elimination
2. Ketone
2. Alkyne
-carbon contains double bond to oxygen; single
-Addition and Elimination
bonds to both carbons
3. Arene (aromatic ring)
3. Carboxylic acid
--Substitution
--carbon contains double bond to oxygen; single
bonds to carbon and OH- (hydroxyl group)
4. Ester
--carbon contains double bond to oxygen; single
bonds to carbon and H + C
5. Thioester
--carbon contains double bond to oxygen; single
bonds to carbon and S + C
6. Amide
7. -carbon contains double bond to oxygen; single
bonds to carbon and nitrogen
8. Acid chloride
9. -carbon contains double bond to oxygen; single
FUNCTIONAL GROUPS W/ CARBON SINGLY BONDED TO AN bonds to carbon and chloride
ELECTRONEGATIVE ATOM
 Strong pull of electrons
 High electronegativity
Examples:
1. Alkyl halide (haloalkane)
-high electronegativity (such as Cl-)
2. Alcohol
-has oxygen w/ a Hydrogen group
3. Ether
-has oxygen found w/in the hydrocarbon
4. Phosphate
-has EN atoms
5. Amine
-EN
-Nitrogen (red)
6. Thiol
-Sulfur
-the same w/ alcohol – usually found in
hydrocarbons in the presence of Hydrogen
7. Sulfide
-has oxygen found w/in the sulfur
8. Disulfide
-2 Sulfur atoms in a carbon chain
- strong (ex. antibodies in the body)
 3. Lecture on Organic Chemistry Part 2

IMPORTANT FUNCTIONAL GROUPS IN ORGANIC

COMPOUNDS
 BE AWARE OF THE STRUCTURES!
Ex. Alkene and alkyne are water insoluble
- An addition of an electronegative atom
like O2 or OH- will result to a water
soluble compound